#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:55:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180202 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/96/7109646.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7109646
loop_
_publ_author_name
'Manolis D. Tzirakis'
'Nicolas Marion'
'W. Bernd Schweizer'
'Francois Diederich'
_publ_section_title
;
 A shape-persistent alleno-acetylenic macrocycle with a modifiable
 periphery: synthesis, chiroptical properties and H-bond-driven
 self-assembly into a homochiral columnar structure
;
_journal_name_full               Chem.Commun.
_journal_page_first              7605
_journal_paper_doi               10.1039/c3cc44101f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C H2 Cl2, C100 H88 O8, 2(C3.5 H8)'
_chemical_formula_sum            'C108 H106 Cl2 O8'
_chemical_formula_weight         1602.83
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.190(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   27.930(3)
_cell_length_b                   8.9770(9)
_cell_length_c                   20.9383(15)
_cell_measurement_reflns_used    5471
_cell_measurement_temperature    100
_cell_measurement_theta_max      49.48
_cell_measurement_theta_min      3.33
_cell_volume                     4894.9(8)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9424
_diffrn_reflns_theta_full        50.08
_diffrn_reflns_theta_max         50.08
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.7686.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
'Flack H D (1983), Acta Cryst. A39, 876-881'
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.408
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.410
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.1055
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2781
_refine_ls_wR_factor_ref         0.2893
_reflns_number_gt                2392
_reflns_number_total             2706
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44101f.txt
_cod_data_source_block           cu_d050412_0m
_cod_original_cell_volume        4894.8(8)
_cod_database_code               7109646
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C61-C60 = C62-C61 = C63-C62
 1.53 with sigma of 0.02
 C57-C56
 1.53 with sigma of 0.02
 C57-C58
 1.53 with sigma of 0.02
 C58-C59
 1.53 with sigma of 0.02
 Cl1-C55 = Cl2-C55
 1.77 with sigma of 0.02
 C60-C62 = C61-C63
 2.45 with sigma of 0.04
 C56-C58
 2.45 with sigma of 0.04
 C57-C59
 2.45 with sigma of 0.04
 Cl1-Cl2
 2.93 with sigma of 0.04
3. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C55(0.5) H55A(0.5) H55B(0.5) C56(0.5) H56A(0.5)
 H56B(0.5) H56C(0.5) C57(0.5) H57A(0.5) H57B(0.5) C58(0.5) H58A(0.5) H58B(0.5)
 C59(0.25) H59A(0.25) H59B(0.25) C60(0.5) H60A(0.5) H60B(0.5) H60C(0.5)
 C61(0.5) H61A(0.5) H61B(0.5) C62(0.5) H62A(0.5) H62B(0.5) C63(0.25) H63A(0.25)
 H63B(0.25)
 Fixed X: C59(0)
 Fixed Z: C59(0)
4.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C61(H61A,
 H61B), C62(H62A,H62B), C63(H63A,H63B)
4.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23), C29(H29), C30(H30), C32(H32),
 C33(H33), C39(H39), C40(H40), C42(H42), C43(H43), C49(H49), C50(H50), C52(H52),
  C53(H53)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C56(H56A,H56B,H56C), C60(H60A,H60B,H60C)
4.d Idealised tetrahedral OH refined as rotating group:
 O24(H24), O34(H34), O44(H44), O54(H54)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.0616(7) 0.342(2) 1.4896(9) 0.221(6) Uani 0.50 1 d PD A -1
Cl2 Cl 0.0018(19) 0.564(5) 1.525(2) 0.41(2) Uiso 0.50 1 d PD A -1
C55 C 0.009(3) 0.463(9) 1.454(2) 0.29(4) Uiso 0.50 1 d PD A -1
H55A H -0.0261 0.3996 1.4274 0.349 Uiso 0.50 1 calc PR A -1
H55B H 0.0156 0.5397 1.4183 0.349 Uiso 0.50 1 calc PR A -1
O24 O -0.1642(5) 0.4149(13) 0.4742(4) 0.128(4) Uani 1 1 d . . .
H24 H -0.1438 0.3231 0.4838 0.193 Uiso 1 1 calc R . .
O34 O -0.0922(6) 0.8590(17) 0.4540(4) 0.173(6) Uani 1 1 d . . .
H34 H -0.1219 0.8171 0.4173 0.260 Uiso 1 1 calc R . .
O44 O 0.0546(4) 0.1048(15) 0.5702(4) 0.122(3) Uani 1 1 d . . .
H44 H 0.0709 0.0096 0.5674 0.183 Uiso 1 1 calc R . .
O54 O 0.1386(3) 0.6053(11) 0.6057(3) 0.090(2) Uani 1 1 d . . .
H54 H 0.1523 0.5217 0.5875 0.134 Uiso 1 1 calc R . .
C1 C -0.2002(3) 0.6251(11) 0.7496(4) 0.044(2) Uani 1 1 d . . .
C2 C -0.1633(3) 0.7009(11) 0.7410(3) 0.045(2) Uani 1 1 d . . .
C3 C -0.1238(3) 0.7742(12) 0.7347(4) 0.053(2) Uani 1 1 d . . .
C4 C -0.0757(4) 0.6968(14) 0.7572(4) 0.061(3) Uani 1 1 d . . .
C5 C -0.0360(4) 0.6356(15) 0.7769(4) 0.067(3) Uani 1 1 d . . .
C6 C 0.0116(4) 0.5585(15) 0.8015(5) 0.075(4) Uani 1 1 d . . .
C7 C 0.0524(3) 0.4905(16) 0.8278(5) 0.074(3) Uani 1 1 d . . .
C8 C 0.0971(4) 0.4161(15) 0.8581(4) 0.065(3) Uani 1 1 d . . .
C9 C 0.1407(4) 0.4938(13) 0.8935(5) 0.065(3) Uani 1 1 d . . .
C10 C 0.1822(3) 0.5663(11) 0.9290(4) 0.048(2) Uani 1 1 d . . .
C11 C 0.1921(3) 0.5892(11) 0.9997(5) 0.052(2) Uani 1 1 d . . .
C12 C 0.1986(3) 0.6096(12) 1.0585(5) 0.051(2) Uani 1 1 d . . .
C13 C 0.2040(3) 0.6252(12) 1.1266(5) 0.057(2) Uani 1 1 d . . .
C14 C 0.2046(3) 0.6294(12) 1.1854(5) 0.056(2) Uani 1 1 d . . .
C15 C -0.2379(4) 0.5275(13) 0.6947(4) 0.062(3) Uani 1 1 d . . .
C16 C -0.2916(4) 0.5991(17) 0.6729(6) 0.090(4) Uani 1 1 d . . .
H16A H -0.3040 0.6030 0.7167 0.135 Uiso 1 1 calc R . .
H16B H -0.3188 0.5330 0.6322 0.135 Uiso 1 1 calc R . .
H16C H -0.2901 0.7119 0.6544 0.135 Uiso 1 1 calc R . .
C17 C -0.2403(6) 0.3717(14) 0.7264(6) 0.094(4) Uani 1 1 d . . .
H17A H -0.2024 0.3203 0.7435 0.141 Uiso 1 1 calc R . .
H17B H -0.2676 0.3011 0.6879 0.141 Uiso 1 1 calc R . .
H17C H -0.2526 0.3848 0.7698 0.141 Uiso 1 1 calc R . .
C18 C -0.2196(4) 0.5071(14) 0.6340(5) 0.070(3) Uani 1 1 d . . .
C19 C -0.1737(5) 0.4360(14) 0.6453(5) 0.084(3) Uani 1 1 d . . .
H19 H -0.1516 0.4005 0.6969 0.101 Uiso 1 1 calc R . .
C20 C -0.1537(7) 0.4065(15) 0.5932(8) 0.114(5) Uani 1 1 d . . .
H20 H -0.1163 0.3562 0.6054 0.136 Uiso 1 1 calc R . .
C21 C -0.1824(7) 0.4427(16) 0.5280(6) 0.095(4) Uani 1 1 d . . .
C22 C -0.2297(5) 0.5144(19) 0.5120(5) 0.091(4) Uani 1 1 d . . .
H22 H -0.2517 0.5439 0.4595 0.109 Uiso 1 1 calc R . .
C23 C -0.2497(5) 0.5500(15) 0.5665(5) 0.091(4) Uani 1 1 d . . .
H23 H -0.2859 0.6067 0.5552 0.109 Uiso 1 1 calc R . .
C25 C -0.1251(3) 0.9302(13) 0.7054(4) 0.062(3) Uani 1 1 d . . .
C26 C -0.0841(4) 1.0220(16) 0.7585(5) 0.083(4) Uani 1 1 d . . .
H26A H -0.0938 1.0337 0.8042 0.124 Uiso 1 1 calc R . .
H26B H -0.0819 1.1318 0.7376 0.124 Uiso 1 1 calc R . .
H26C H -0.0471 0.9662 0.7718 0.124 Uiso 1 1 calc R . .
C27 C -0.1781(4) 0.9961(12) 0.6928(5) 0.067(3) Uani 1 1 d . . .
H27A H -0.2075 0.9227 0.6589 0.101 Uiso 1 1 calc R . .
H27B H -0.1809 1.1053 0.6689 0.101 Uiso 1 1 calc R . .
H27C H -0.1838 1.0073 0.7414 0.101 Uiso 1 1 calc R . .
C28 C -0.1142(4) 0.9148(12) 0.6400(4) 0.061(3) Uani 1 1 d . . .
C29 C -0.0768(5) 0.994(2) 0.6282(5) 0.111(5) Uani 1 1 d . . .
H29 H -0.0550 1.0746 0.6655 0.133 Uiso 1 1 calc R . .
C30 C -0.0656(8) 0.972(3) 0.5677(8) 0.168(10) Uani 1 1 d . . .
H30 H -0.0321 1.0186 0.5609 0.201 Uiso 1 1 calc R . .
C31 C -0.1045(7) 0.878(2) 0.5139(6) 0.124(6) Uani 1 1 d . . .
C32 C -0.1389(4) 0.8040(15) 0.5254(5) 0.079(3) Uani 1 1 d . . .
H32 H -0.1624 0.7265 0.4876 0.095 Uiso 1 1 calc R . .
C33 C -0.1464(4) 0.8230(14) 0.5877(5) 0.072(3) Uani 1 1 d . . .
H33 H -0.1778 0.7656 0.5957 0.086 Uiso 1 1 calc R . .
C35 C 0.0975(4) 0.2487(17) 0.8510(5) 0.080(4) Uani 1 1 d . . .
C36 C 0.1514(6) 0.1835(18) 0.8894(7) 0.121(6) Uani 1 1 d . . .
H36A H 0.1784 0.2291 0.8678 0.182 Uiso 1 1 calc R . .
H36B H 0.1500 0.0626 0.8840 0.182 Uiso 1 1 calc R . .
H36C H 0.1638 0.2126 0.9435 0.182 Uiso 1 1 calc R . .
C37 C 0.0577(5) 0.185(2) 0.8775(7) 0.119(6) Uani 1 1 d . . .
H37A H 0.0595 0.2447 0.9238 0.179 Uiso 1 1 calc R . .
H37B H 0.0654 0.0674 0.8893 0.179 Uiso 1 1 calc R . .
H37C H 0.0195 0.1982 0.8385 0.179 Uiso 1 1 calc R . .
C38 C 0.0860(3) 0.2097(16) 0.7755(5) 0.078(3) Uani 1 1 d . . .
C39 C 0.0954(4) 0.307(2) 0.7301(5) 0.095(4) Uani 1 1 d . . .
H39 H 0.1124 0.4138 0.7493 0.114 Uiso 1 1 calc R . .
C40 C 0.0842(4) 0.275(2) 0.6613(7) 0.097(4) Uani 1 1 d . . .
H40 H 0.0904 0.3564 0.6270 0.117 Uiso 1 1 calc R . .
C41 C 0.0656(5) 0.142(2) 0.6395(7) 0.093(4) Uani 1 1 d . . .
C42 C 0.0561(5) 0.0340(19) 0.6797(7) 0.104(4) Uani 1 1 d . . .
H42 H 0.0415 -0.0741 0.6592 0.124 Uiso 1 1 calc R . .
C43 C 0.0663(5) 0.0706(17) 0.7502(6) 0.091(4) Uani 1 1 d . . .
H43 H 0.0586 -0.0101 0.7836 0.109 Uiso 1 1 calc R . .
C45 C 0.2217(3) 0.6138(11) 0.8975(4) 0.051(2) Uani 1 1 d . . .
C46 C 0.2683(3) 0.5159(14) 0.9288(4) 0.059(3) Uani 1 1 d . . .
H46A H 0.2831 0.5297 0.9842 0.089 Uiso 1 1 calc R . .
H46B H 0.2977 0.5475 0.9085 0.089 Uiso 1 1 calc R . .
H46C H 0.2576 0.3999 0.9161 0.089 Uiso 1 1 calc R . .
C47 C 0.2371(4) 0.7775(12) 0.9192(4) 0.062(3) Uani 1 1 d . . .
H47A H 0.2033 0.8485 0.9002 0.093 Uiso 1 1 calc R . .
H47B H 0.2653 0.8145 0.8978 0.093 Uiso 1 1 calc R . .
H47C H 0.2537 0.7845 0.9749 0.093 Uiso 1 1 calc R . .
C48 C 0.1984(3) 0.6063(12) 0.8188(4) 0.055(2) Uani 1 1 d . . .
C49 C 0.1578(4) 0.6948(14) 0.7843(5) 0.070(3) Uani 1 1 d . . .
H49 H 0.1414 0.7672 0.8122 0.085 Uiso 1 1 calc R . .
C50 C 0.1374(4) 0.6919(16) 0.7130(5) 0.079(3) Uani 1 1 d . . .
H50 H 0.1044 0.7598 0.6855 0.095 Uiso 1 1 calc R . .
C51 C 0.1592(4) 0.6025(15) 0.6772(4) 0.067(3) Uani 1 1 d . . .
C52 C 0.1985(4) 0.5143(13) 0.7102(4) 0.061(3) Uani 1 1 d . . .
H52 H 0.2146 0.4422 0.6818 0.073 Uiso 1 1 calc R . .
C53 C 0.2190(3) 0.5149(12) 0.7819(4) 0.056(2) Uani 1 1 d . . .
H53 H 0.2512 0.4436 0.8087 0.068 Uiso 1 1 calc R . .
C56 C 0.1240(10) 0.271(4) 0.1012(14) 0.105(8) Uiso 0.50 1 d PD B 1
H56A H 0.1230 0.2798 0.0488 0.157 Uiso 0.50 1 calc PR B 1
H56B H 0.1219 0.1545 0.1141 0.157 Uiso 0.50 1 calc PR B 1
H56C H 0.1596 0.3195 0.1362 0.157 Uiso 0.50 1 calc PR B 1
C57 C 0.0789(14) 0.355(7) 0.1073(19) 0.25(3) Uiso 0.50 1 d PD B 1
H57A H 0.0545 0.2748 0.1202 0.294 Uiso 0.50 1 calc PR B 1
H57B H 0.0935 0.4323 0.1500 0.294 Uiso 0.50 1 calc PR B 1
C58 C 0.0464(14) 0.440(5) 0.045(2) 0.202(19) Uiso 0.50 1 d PD B 1
H58A H 0.0697 0.4715 0.0156 0.242 Uiso 0.50 1 calc PR B 1
H58B H 0.0329 0.5417 0.0617 0.242 Uiso 0.50 1 calc PR B 1
C59 C 0.0000 0.349(8) 0.0000 0.17(2) Uiso 0.50 2 d SPD . 1
H59A H -0.0125 0.2772 0.0329 0.204 Uiso 0.25 1 calc PR . 1
H59B H 0.0125 0.2771 -0.0329 0.204 Uiso 0.25 1 calc PR . 1
C60 C 0.0785(17) 0.856(8) -0.0036(19) 0.191(17) Uiso 0.50 1 d PD . .
H60A H 0.0511 0.7751 -0.0352 0.286 Uiso 0.50 1 calc PR . .
H60B H 0.1172 0.8249 0.0002 0.286 Uiso 0.50 1 calc PR . .
H60C H 0.0693 0.9662 -0.0269 0.286 Uiso 0.50 1 calc PR . .
C61 C 0.0757(11) 0.860(6) 0.0676(17) 0.174(16) Uiso 0.50 1 d PD . .
H61A H 0.0941 0.9595 0.0953 0.209 Uiso 0.50 1 calc PR . .
H61B H 0.0942 0.7618 0.0971 0.209 Uiso 0.50 1 calc PR . .
C62 C 0.0172(12) 0.860(5) 0.0534(19) 0.171(15) Uiso 0.50 1 d PD . .
H62A H 0.0090 0.8342 0.0994 0.205 Uiso 0.50 1 calc PR . .
H62B H -0.0006 0.9661 0.0323 0.205 Uiso 0.50 1 calc PR . .
C63 C 0.0000 0.733(6) 0.0000 0.17(2) Uiso 0.50 2 d SPD . .
H63A H -0.0313 0.6650 0.0033 0.208 Uiso 0.25 1 calc PR . .
H63B H 0.0313 0.6650 -0.0033 0.208 Uiso 0.25 1 calc PR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl1 C55 Cl2 107(2) . .
Cl1 C55 H55A 110.4 . .
Cl1 C55 H55B 110.4 . .
Cl2 C55 H55A 110.4 . .
Cl2 C55 H55B 110.4 . .
H55A C55 H55B 108.6 . .
C21 O24 H24 109.5 . .
C31 O34 H34 109.5 . .
C41 O44 H44 109.5 . .
C51 O54 H54 109.5 . .
C2 C1 C14 118.0(7) . 2_557
C2 C1 C15 124.2(7) . .
C14 C1 C15 117.8(8) 2_557 .
C1 C2 C3 177.0(9) . .
C2 C3 C4 116.1(10) . .
C2 C3 C25 126.4(9) . .
C4 C3 C25 117.5(8) . .
C5 C4 C3 178.4(11) . .
C4 C5 C6 178.5(12) . .
C7 C6 C5 175.0(9) . .
C6 C7 C8 178.6(9) . .
C7 C8 C9 119.5(12) . .
C7 C8 C35 118.9(10) . .
C9 C8 C35 121.6(10) . .
C10 C9 C8 178.2(9) . .
C9 C10 C11 117.8(8) . .
C9 C10 C45 121.4(7) . .
C11 C10 C45 120.5(7) . .
C12 C11 C10 177.5(8) . .
C11 C12 C13 176.2(10) . .
C14 C13 C12 173.5(10) . .
C13 C14 C1 173.6(9) . 2_557
C1 C15 C16 108.5(9) . .
C1 C15 C17 108.6(8) . .
C1 C15 C18 110.2(8) . .
C16 C15 C17 108.2(9) . .
C18 C15 C16 112.5(8) . .
C18 C15 C17 108.7(9) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C19 C18 C15 118.7(9) . .
C19 C18 C23 118.6(11) . .
C23 C18 C15 122.5(11) . .
C18 C19 H19 118.1 . .
C18 C19 C20 123.8(13) . .
C20 C19 H19 118.1 . .
C19 C20 H20 120.7 . .
C21 C20 C19 118.6(16) . .
C21 C20 H20 120.7 . .
C20 C21 O24 120.7(15) . .
C20 C21 C22 121.2(11) . .
C22 C21 O24 118.1(12) . .
C21 C22 H22 119.9 . .
C21 C22 C23 120.3(10) . .
C23 C22 H22 119.9 . .
C18 C23 C22 117.4(13) . .
C18 C23 H23 121.3 . .
C22 C23 H23 121.3 . .
C26 C25 C3 107.6(8) . .
C26 C25 C27 110.2(9) . .
C27 C25 C3 107.9(8) . .
C28 C25 C3 107.3(8) . .
C28 C25 C26 111.4(8) . .
C28 C25 C27 112.2(8) . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C29 C28 C25 122.6(9) . .
C29 C28 C33 118.8(9) . .
C33 C28 C25 118.4(9) . .
C28 C29 H29 119.3 . .
C28 C29 C30 121.5(11) . .
C30 C29 H29 119.3 . .
C29 C30 H30 122.9 . .
C29 C30 C31 114.2(12) . .
C31 C30 H30 122.9 . .
O34 C31 C30 112.7(12) . .
C32 C31 O34 123.1(13) . .
C32 C31 C30 123.1(11) . .
C31 C32 H32 120.3 . .
C31 C32 C33 119.4(11) . .
C33 C32 H32 120.3 . .
C28 C33 C32 121.8(10) . .
C28 C33 H33 119.1 . .
C32 C33 H33 119.1 . .
C8 C35 C36 111.6(10) . .
C8 C35 C37 107.7(12) . .
C8 C35 C38 108.7(10) . .
C36 C35 C38 104.5(10) . .
C37 C35 C36 111.9(12) . .
C37 C35 C38 112.5(9) . .
C35 C36 H36A 109.5 . .
C35 C36 H36B 109.5 . .
C35 C36 H36C 109.5 . .
H36A C36 H36B 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
C35 C37 H37A 109.5 . .
C35 C37 H37B 109.5 . .
C35 C37 H37C 109.5 . .
H37A C37 H37B 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C39 C38 C35 122.8(12) . .
C39 C38 C43 117.0(11) . .
C43 C38 C35 120.2(12) . .
C38 C39 H39 118.2 . .
C38 C39 C40 123.7(14) . .
C40 C39 H39 118.2 . .
C39 C40 H40 121.4 . .
C41 C40 C39 117.3(14) . .
C41 C40 H40 121.4 . .
C40 C41 O44 118.8(13) . .
C40 C41 C42 124.6(13) . .
C42 C41 O44 116.5(15) . .
C41 C42 H42 121.3 . .
C41 C42 C43 117.3(15) . .
C43 C42 H42 121.3 . .
C38 C43 C42 120.1(13) . .
C38 C43 H43 120.0 . .
C42 C43 H43 120.0 . .
C10 C45 C47 107.7(7) . .
C10 C45 C48 111.0(7) . .
C46 C45 C10 107.0(7) . .
C46 C45 C47 108.6(7) . .
C46 C45 C48 113.8(7) . .
C48 C45 C47 108.7(7) . .
C45 C46 H46A 109.5 . .
C45 C46 H46B 109.5 . .
C45 C46 H46C 109.5 . .
H46A C46 H46B 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C45 C47 H47A 109.5 . .
C45 C47 H47B 109.5 . .
C45 C47 H47C 109.5 . .
H47A C47 H47B 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C49 C48 C45 119.4(8) . .
C49 C48 C53 119.0(8) . .
C53 C48 C45 121.6(8) . .
C48 C49 H49 120.1 . .
C48 C49 C50 119.9(10) . .
C50 C49 H49 120.1 . .
C49 C50 H50 120.0 . .
C51 C50 C49 120.1(10) . .
C51 C50 H50 120.0 . .
C50 C51 O54 118.5(10) . .
C52 C51 O54 120.8(9) . .
C52 C51 C50 120.6(8) . .
C51 C52 H52 120.1 . .
C51 C52 C53 119.8(9) . .
C53 C52 H52 120.1 . .
C48 C53 C52 120.5(9) . .
C48 C53 H53 119.7 . .
C52 C53 H53 119.7 . .
C56 C57 H57A 108.2 . .
C56 C57 H57B 108.2 . .
H57A C57 H57B 107.4 . .
C58 C57 C56 116(3) . .
C58 C57 H57A 108.2 . .
C58 C57 H57B 108.2 . .
C57 C58 H58A 109.2 . .
C57 C58 H58B 109.2 . .
C57 C58 C59 112(3) . .
H58A C58 H58B 107.9 . .
C59 C58 H58A 109.2 . .
C59 C58 H58B 109.2 . .
C58 C59 C58 116(4) . 2
C58 C59 H59A 108.3 . .
C58 C59 H59A 108.3 2 .
C58 C59 H59B 108.3 . .
C58 C59 H59B 108.3 2 .
H59A C59 H59B 107.4 . .
H60A C60 H60B 109.5 . .
H60A C60 H60C 109.5 . .
H60B C60 H60C 109.5 . .
C61 C60 H60A 109.5 . .
C61 C60 H60B 109.5 . .
C61 C60 H60C 109.5 . .
C60 C61 H61A 111.0 . .
C60 C61 H61B 111.0 . .
C60 C61 C62 104(2) . .
H61A C61 H61B 109.0 . .
C62 C61 H61A 111.0 . .
C62 C61 H61B 111.0 . .
C61 C62 H62A 111.9 . .
C61 C62 H62B 111.9 . .
H62A C62 H62B 109.6 . .
C63 C62 C61 100(2) . .
C63 C62 H62A 111.9 . .
C63 C62 H62B 111.9 . .
C62 C63 C62 85(4) . 2
C62 C63 H63A 114.5 . .
C62 C63 H63A 114.5 2 .
C62 C63 H63B 114.5 . .
C62 C63 H63B 114.5 2 .
H63A C63 H63B 111.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C55 1.77(2) .
Cl2 C55 1.79(2) .
C55 H55A 1.0900 .
C55 H55B 1.0900 .
O24 H24 0.9801 .
O24 C21 1.415(15) .
O34 H34 0.9801 .
O34 C31 1.425(16) .
O44 H44 0.9801 .
O44 C41 1.410(15) .
O54 H54 0.9801 .
O54 C51 1.398(11) .
C1 C2 1.301(13) .
C1 C14 1.410(13) 2_557
C1 C15 1.523(14) .
C2 C3 1.332(13) .
C3 C4 1.432(16) .
C3 C25 1.523(16) .
C4 C5 1.172(14) .
C5 C6 1.420(17) .
C6 C7 1.233(15) .
C7 C8 1.354(16) .
C8 C9 1.367(16) .
C8 C35 1.510(19) .
C9 C10 1.302(14) .
C10 C11 1.419(13) .
C10 C45 1.537(12) .
C11 C12 1.192(12) .
C12 C13 1.384(16) .
C13 C14 1.226(12) .
C14 C1 1.410(13) 2_557
C15 C16 1.543(16) .
C15 C17 1.559(17) .
C15 C18 1.543(14) .
C16 H16A 1.0899 .
C16 H16B 1.0899 .
C16 H16C 1.0899 .
C17 H17A 1.0899 .
C17 H17B 1.0899 .
C17 H17C 1.0899 .
C18 C19 1.373(16) .
C18 C23 1.413(15) .
C19 H19 1.0800 .
C19 C20 1.420(16) .
C20 H20 1.0800 .
C20 C21 1.35(2) .
C21 C22 1.397(19) .
C22 H22 1.0800 .
C22 C23 1.476(17) .
C23 H23 1.0800 .
C25 C26 1.519(14) .
C25 C27 1.526(14) .
C25 C28 1.513(13) .
C26 H26A 1.0899 .
C26 H26B 1.0899 .
C26 H26C 1.0899 .
C27 H27A 1.0899 .
C27 H27B 1.0899 .
C27 H27C 1.0899 .
C28 C29 1.356(15) .
C28 C33 1.406(14) .
C29 H29 1.0800 .
C29 C30 1.424(18) .
C30 H30 1.0800 .
C30 C31 1.51(2) .
C31 C32 1.262(18) .
C32 H32 1.0800 .
C32 C33 1.405(15) .
C33 H33 1.0800 .
C35 C36 1.543(18) .
C35 C37 1.521(17) .
C35 C38 1.537(16) .
C36 H36A 1.0899 .
C36 H36B 1.0899 .
C36 H36C 1.0899 .
C37 H37A 1.0899 .
C37 H37B 1.0899 .
C37 H37C 1.0899 .
C38 C39 1.384(19) .
C38 C43 1.390(19) .
C39 H39 1.0800 .
C39 C40 1.390(17) .
C40 H40 1.0800 .
C40 C41 1.32(2) .
C41 C42 1.37(2) .
C42 H42 1.0800 .
C42 C43 1.437(17) .
C43 H43 1.0800 .
C45 C46 1.509(13) .
C45 C47 1.553(16) .
C45 C48 1.539(12) .
C46 H46A 1.0899 .
C46 H46B 1.0899 .
C46 H46C 1.0899 .
C47 H47A 1.0899 .
C47 H47B 1.0899 .
C47 H47C 1.0899 .
C48 C49 1.359(14) .
C48 C53 1.386(13) .
C49 H49 1.0800 .
C49 C50 1.394(13) .
C50 H50 1.0800 .
C50 C51 1.381(16) .
C51 C52 1.325(14) .
C52 H52 1.0800 .
C52 C53 1.400(12) .
C53 H53 1.0800 .
C56 H56A 1.0899 .
C56 H56B 1.0899 .
C56 H56C 1.0899 .
C56 C57 1.51(2) .
C57 H57A 1.0900 .
C57 H57B 1.0900 .
C57 C58 1.50(2) .
C58 H58A 1.0900 .
C58 H58B 1.0900 .
C58 C59 1.54(2) .
C59 C58 1.54(2) 2
C59 H59A 1.0900 .
C59 H59B 1.0900 .
C60 H60A 1.0899 .
C60 H60B 1.0899 .
C60 H60C 1.0899 .
C60 C61 1.52(2) .
C61 H61A 1.0900 .
C61 H61B 1.0900 .
C61 C62 1.55(2) .
C62 H62A 1.0900 .
C62 H62B 1.0900 .
C62 C63 1.55(2) .
C63 C62 1.55(2) 2
C63 H63A 1.0900 .
C63 H63B 1.0900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O24 C21 C22 C23 -178.2(11) . .
O34 C31 C32 C33 176.0(16) . .
O44 C41 C42 C43 -179.0(10) . .
O54 C51 C52 C53 179.1(9) . .
C1 C2 C3 C4 23(18) . .
C1 C2 C3 C25 -158(17) . .
C1 C15 C18 C19 62.9(13) . .
C1 C15 C18 C23 -121.3(11) . .
C2 C1 C15 C16 -112.3(10) . .
C2 C1 C15 C17 130.3(10) . .
C2 C1 C15 C18 11.2(14) . .
C2 C3 C4 C5 -108(44) . .
C2 C3 C25 C26 125.9(9) . .
C2 C3 C25 C27 7.0(11) . .
C2 C3 C25 C28 -114.1(9) . .
C3 C4 C5 C6 97(66) . .
C3 C25 C28 C29 -127.0(12) . .
C3 C25 C28 C33 57.5(12) . .
C4 C3 C25 C26 -54.9(10) . .
C4 C3 C25 C27 -173.7(7) . .
C4 C3 C25 C28 65.1(9) . .
C4 C5 C6 C7 -44(52) . .
C5 C6 C7 C8 -8(68) . .
C6 C7 C8 C9 -80(57) . .
C6 C7 C8 C35 101(57) . .
C7 C8 C9 C10 106(35) . .
C7 C8 C35 C36 -179.5(10) . .
C7 C8 C35 C37 -56.3(12) . .
C7 C8 C35 C38 65.8(12) . .
C8 C9 C10 C11 -17(35) . .
C8 C9 C10 C45 158(34) . .
C8 C35 C38 C39 24.3(14) . .
C8 C35 C38 C43 -157.0(10) . .
C9 C8 C35 C36 1.3(15) . .
C9 C8 C35 C37 124.5(10) . .
C9 C8 C35 C38 -113.4(9) . .
C9 C10 C11 C12 -42(24) . .
C9 C10 C45 C46 -108.1(10) . .
C9 C10 C45 C47 135.3(9) . .
C9 C10 C45 C48 16.5(12) . .
C10 C11 C12 C13 64(31) . .
C10 C45 C48 C49 62.5(12) . .
C10 C45 C48 C53 -119.8(10) . .
C11 C10 C45 C46 66.4(11) . .
C11 C10 C45 C47 -50.2(10) . .
C11 C10 C45 C48 -169.0(8) . .
C11 C12 C13 C14 -15(21) . .
C12 C13 C14 C1 -7(16) . 2_557
C14 C1 C2 C3 61(18) 2_557 .
C14 C1 C15 C16 69.9(11) 2_557 .
C14 C1 C15 C17 -47.5(12) 2_557 .
C14 C1 C15 C18 -166.6(9) 2_557 .
C15 C1 C2 C3 -117(17) . .
C15 C18 C19 C20 177.9(11) . .
C15 C18 C23 C22 -175.5(11) . .
C16 C15 C18 C19 -175.9(11) . .
C16 C15 C18 C23 -0.1(14) . .
C17 C15 C18 C19 -56.1(13) . .
C17 C15 C18 C23 119.7(12) . .
C18 C19 C20 C21 -4(2) . .
C19 C18 C23 C22 0.3(16) . .
C19 C20 C21 O24 -179.7(12) . .
C19 C20 C21 C22 3(2) . .
C20 C21 C22 C23 -1(2) . .
C21 C22 C23 C18 -0.8(18) . .
C23 C18 C19 C20 1.9(18) . .
C25 C3 C4 C5 72(44) . .
C25 C28 C29 C30 176.9(16) . .
C25 C28 C33 C32 179.6(10) . .
C26 C25 C28 C29 -9.5(16) . .
C26 C25 C28 C33 175.0(11) . .
C27 C25 C28 C29 114.6(13) . .
C27 C25 C28 C33 -60.9(13) . .
C28 C29 C30 C31 11(3) . .
C29 C28 C33 C32 3.9(18) . .
C29 C30 C31 O34 179.8(19) . .
C29 C30 C31 C32 -12(3) . .
C30 C31 C32 C33 9(3) . .
C31 C32 C33 C28 -5(2) . .
C33 C28 C29 C30 -8(2) . .
C35 C8 C9 C10 -74(35) . .
C35 C38 C39 C40 -178.4(11) . .
C35 C38 C43 C42 -179.4(10) . .
C36 C35 C38 C39 -95.0(14) . .
C36 C35 C38 C43 83.7(13) . .
C37 C35 C38 C39 143.5(13) . .
C37 C35 C38 C43 -37.8(17) . .
C38 C39 C40 C41 -3(2) . .
C39 C38 C43 C42 -0.6(17) . .
C39 C40 C41 O44 -178.9(11) . .
C39 C40 C41 C42 1(2) . .
C40 C41 C42 C43 1(2) . .
C41 C42 C43 C38 -1.3(17) . .
C43 C38 C39 C40 2.8(18) . .
C45 C10 C11 C12 144(23) . .
C45 C48 C49 C50 178.2(10) . .
C45 C48 C53 C52 -177.5(9) . .
C46 C45 C48 C49 -176.9(10) . .
C46 C45 C48 C53 0.9(13) . .
C47 C45 C48 C49 -55.7(11) . .
C47 C45 C48 C53 122.0(10) . .
C48 C49 C50 C51 -1.8(18) . .
C49 C48 C53 C52 0.3(15) . .
C49 C50 C51 O54 -178.4(10) . .
C49 C50 C51 C52 2.6(19) . .
C50 C51 C52 C53 -1.9(17) . .
C51 C52 C53 C48 0.4(15) . .
C53 C48 C49 C50 0.3(16) . .
C56 C57 C58 C59 94(5) . .
C57 C58 C59 C58 155(4) . 2
C60 C61 C62 C63 47(5) . .
C61 C62 C63 C62 -101(3) . 2
